WO2019138355A1 - Composition, bacterial repelling coating and method for forming the same, and article having bacterial repelling coating - Google Patents
Composition, bacterial repelling coating and method for forming the same, and article having bacterial repelling coating Download PDFInfo
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- WO2019138355A1 WO2019138355A1 PCT/IB2019/050196 IB2019050196W WO2019138355A1 WO 2019138355 A1 WO2019138355 A1 WO 2019138355A1 IB 2019050196 W IB2019050196 W IB 2019050196W WO 2019138355 A1 WO2019138355 A1 WO 2019138355A1
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
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- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
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- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06147—Dipeptides with the first amino acid being heterocyclic and His-amino acid; Derivatives thereof
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0812—Tripeptides with the first amino acid being neutral and aromatic or cycloaliphatic
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0815—Tripeptides with the first amino acid being basic
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- C07K5/08—Tripeptides
- C07K5/0819—Tripeptides with the first amino acid being acidic
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
- C07K5/1008—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
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- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1019—Tetrapeptides with the first amino acid being basic
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1024—Tetrapeptides with the first amino acid being heterocyclic
Definitions
- the present disclosure relates to a composition comprising a lipid-peptide compound which has bacterial repelling property, a bacterial repelling coating and a method for forming the same, and an article having a bacterial repelling coating comprising a lipid-peptide compound.
- incorporation of a material that prevents or suppresses attachment of bacteria onto a surface imparts bacterial repelling property or antibacterial property to those surfaces.
- surfaces which can be treated with material that prevents or suppresses attachment of bacteria include the external part and the internal part of a living body, for example, the skin, the interior of the oral cavity etc., or into the surfaces of articles such as medical instruments, medical facilities, tableware, sanitary goods, and nursing care equipment, by coating, kneading or the like
- Patent Document 1 JP-A-2011-153101 describes "an oral agent for preventing attachment of microorganisms, comprising a phosphorylcholine group-containing polymer
- PC polymer as a microorganism attachment preventing ingredient, a water-soluble polysaccharide as a binder ingredient, and a poly(meth)acrylic acid derivative as a compatibilizing ingredient.
- Patent Document 2 JP-A-2016-175956 describes "a bacterial repelling material comprising a poly acetal resin (A) containing an ester-terminal group, represented by the following formula, wherein the ester-terminal group is contained at a ratio of 20 pmol or less per 1 g of the polyacetal resin (A).
- RCOO- wherein R represents a hydrogen atom or an alkyl group
- Patent Document 3 JT-A-2009-523890 describes "a curable antibacterial film forming composition, comprising a polymer matrix, a carrier solvent, and at least one long-chain compound comprising a functional group capable of forming a chemical bond with the matrix when the carrier solvent is vaporized, and the composition is dried or cured, wherein the functional group is selected from the group consisting of amine, thiol, carboxyl, aldehyde, hydroxyl and a combination thereof, the at least one long-chain compound is non-leachable when the composition is dried or cured, has a sufficient length for protruding into an organic sediment that was deposited on the surface of the curable composition with time, and over the sediment, permeates a cellular wall of a
- microorganism and can inhibit microorganism colony formation on the surface of the curable composition.
- the present disclosure provides a material that can impart excellent bacterial repelling property to a variety of surfaces.
- antibacterial repelling property means physical property of a material that suppresses or prevents a
- microorganism from being attached to the surface.
- a bacterial repelling composition comprising a structure of a self-organized lipid-peptide compound wherein the lipid-peptide compound is represented by the formula (1):
- RCOP (1) wherein R represents an aliphatic group having 9 to 23 carbon atoms, and P represents a peptide moiety comprising an amino acid sequence of 2 to 4 amino acids.
- the composition also comprises not less than 30% water.
- the bacterial repelling composition comprises an amino acid sequence of 2 to 4 amino acids, wherein the 2 to 4 amino acids are selected from the group of amino acids consisting of alanine (Ala), glutamic acid (Glu), glycine (Gly), histidine (His), Asparagine (Asn), glutamine (Gln), tryptophan (Trp), Tyrosine (Tyr).
- the bacterial repelling composition comprises a fatty acid residue portion RCO, which is composed of R and an adjacent carbonyl group, comprises a lauroyl group, a dodecylcarbonyl group, myristoyl group, a tetradecyl carbonyl group, a palmitoyl group, a margaroyl group, an oleoyl group, an elaidoyl group, a linoleoyl group, a stearoyl group, a vaccenoyl group, an octadecyl carbonyl group, an arachidoyl group, an eicosylcarbonyl group, a behenoyl group, an erucanoyl group, a docosylcarbonyl group, a lignoceroyl group, or a nervonoyl.
- RCO fatty acid residue portion
- a method for forming a bacterial repelling coating comprising applying the bacterial repelling composition to the surface.
- a bacterial repelling coating comprising a structure of a self-organized lipid-peptide compound.
- a bacterial repelling article comprising a base material, and a bacterial repelling coating comprising a structure of a self-organized lipid-peptide compound, the bacterial repelling coating being attached to the surface of the base material.
- Abacterial repelling composition in accordance with one embodiment comprises a structure of a self-organized lipid-peptide compound.
- the lipid- peptide compound has a hydrophobic part composed of a fatty acid residue and a hydrophilic part composed of a peptide moiety. While not wishing to be bound by theory, it is believed that a self-organized structure is formed by association of a plurality of lipid-peptide compounds.
- the self-organized structure may have a variety of shapes, and examples thereof include a spherical shape, a plate shape, a layer shape, a pillar shape, a fibrous shape and the like.
- the structure of a self-organized lipid- peptide compound is fibrous, for example, a nano-fiber having a full length of an order of magnitude of nanometers.
- lipid-peptide compound forming the self-organized structure a compound represented by the following formula (1) or a pharmaceutically acceptable salt thereof can be used.
- R represents an aliphatic group having 9 to 23 carbon atoms. It is desirable that R is a straight aliphatic group having 11 to 23 carbon atoms, optionally having 0 to 2 unsaturated bonds.
- Examples of the fatty acid residue RCO which is composed of R and an adjacent carbonyl group, include a lauroyl group, a dodecyl carbonyl group, myristoyl group, a tetradecyl carbonyl group, a palmitoyl group, a margaroyl group, an oleoyl group, an elaidoyl group, a linoleoyl group, a stearoyl group, a vaccenoyl group, an
- the fatty acid residue portion RCO which is composed of R and an adjacent carbonyl group, particularly includes a lauroyl group, a myristoyl group, a palmitoyl group, a margaroyl group, an oleoyl group, an elaidoyl group, a stearoyl group, or a behenoyl group.
- P represents a peptide moiety composed of a sequence of 2 to 4 amino acids.
- an a-amino acid can be used as an amino acid constituting the peptide moiety P.
- the a-amino acid has the optical activity, it may be either a D type or an L type, and it is advantageous that all amino acids constituting the peptide moiety are a D type or an L type.
- a-amino acid examples include aliphatic amino acids such as Gly, Ala, Val, Leu and Ile, hydroxy group-containing amino acids such as Ser and Thr, sulfur- containing amino acids such as Cys and Met, aromatic amino acids such as Phe, Tyr and Trp, amino acids such as Pro, amide group-containing amino acids such as Asn and Gln, acidic amino acids such as Asp and Glu, basic amino acids such as Lys, His and Arg, and the like.
- basic amino acids can be used as the a-amino acid constituting the peptide moiety P.
- P represents a peptide moiety composed of a sequence of 2 to 4 amino acids, wherein the 2 to 4 amino acids are selected from the group of amino acids consisting of alanine (Ala), glutamic acid (Glu), glycine (Gly), histidine (His), Asparagine (Asn), glutamine (Gln), tryptophan (Trp), Tyrosine (Tyr).
- the 2 to 4 amino acids are selected from the group of amino acids consisting of alanine (Ala), glutamic acid (Glu), glycine (Gly), histidine (His), Asparagine (Asn), glutamine (Gln), tryptophan (Trp), Tyrosine (Tyr).
- no two amino acids in the sequence of 2 to 4 amino acids are the same amino acid.
- the amino acids in the sequence of 2 to 4 amino acids are all different amino acids according to the list of alanine (Ala), glutamic acid (Glu), glycine (Gly), histidine (His), Asparagine (Asn), glutamine (Gln), tryptophan (Trp), Tyrosine (Tyr).
- at least two of the 2 to 4 amino acids in the sequence of amino acids is the same amino acid, selected from the group of alanine (Ala), glutamic acid (Glu), glycine (Gly), histidine (His), Asparagine (Asn), glutamine (Gln), tryptophan (Trp), Tyrosine (Tyr).
- At least one amino acid in the sequence of 2 to 4 amino acids is selected from the group consisting of glycine, histidine, and lysine. In some embodiments, at least two amino acids in the sequence of 2 to 4 amino acids are selected from the group consisting of glycine, histidine, and lysine.
- Examples of the peptide moiety composed of two amino acids, which is used in the lipid-peptide compound represented by the formula (1), include -Gly-His, -Gly-Gln, - Gly-Asn, -Gly-Trp, -Gly-Lys, -Gly-Tyr, -Gly-Glu, -Gly-Gly, -Ala-His, -Ala-Gln, -Ala- Asn, -Ala-Trp, -Ala-Lys, -Ala- Tyr, -Ala-Glu, -Ala-Gly, -His-Gly, -Gln-Gly, -Asn-Gly, - Trp-Gly, -Lys-Gly, -Tyr-Gly, -Glu-Gly, -His-Ala, -Gln-Ala, -Asn-Ala, -Tr
- the lipid-peptide compound in which the peptide moiety is composed of two amino acids may be: lauroyl-Gly-His, lauroyl-Ala-His, myristoyl-Gly- His, myristoyl-Ala-His, palmitoyl-Gly-His, palmitoyl-Gly-Tyr, palmitoyl-Gly-Glu, palmitoyl-Gly-Lys, palmitoyl-Gly-Gly, palmitoyl-Ala-His, stearoyl-Gly-His, or stearoyl- Ala-His.
- Examples of the peptide moiety composed of three amino acids, which is used in the lipid-peptide compound represented by the formula (1), include -Gly-Gly-His, -Gly- Gly-Gln, -Gly-Gly-Asn, -Gly-Gly-Trp, -Gly-Gly-Lys, -Gly-Gly-Tyr, -Gly-Gly-Glu, -Gly- Gly-Gly, -Gly-Ala-His, -Gly-Ala-Gln, -Gly-Ala-Asn, -Gly-Ala-Trp, -Gly-Ala-Lys, -Ala- Gly-His, -Ala-Gly-Gln, -Ala-Gly-Asn, -Ala-Gly-Trp, -Ala-Gly-Lys, -Ala-Gly-His,
- Examples of the peptide moiety composed of four amino acids, which is used in the lipid-peptide compound represented by the formula (1), include -Gly-Gly-Gly-His, - Gly-Gly-His-Gly, -Gly-His-Gly-Gly, -His-Gly-Gly-Gly, -Gly-Gly-Gly-Lys, -Gly-Gly-Lys- Gly, -Gly-Lys-Gly-Gly, -Lys-Gly-Gly, and the like. These peptide moieties can be appropriately combined with the fatty acid residues to give lipid-peptide compounds.
- the compounds represented by the formula (1) or pharmaceutically acceptable salts thereof can be used alone or can be used by combining two or more of them.
- the lipid-peptide compound is a compound represented by the formula (1):
- RCOP (1) wherein R represents an aliphatic group having 9 to 23 carbon atoms, and P is a two amino acid peptide moiety selected from the group consisting of -Gly-His, -Gly-Gly, and -Gly- Lys or a pharmaceutically acceptable salts thereof.
- the amount of the lipid-peptide compound as a percent of the entire composition can be, for example, 0.01% by mass or more, 0.02% by mass or more, 0.1% by mass or more, 0.2% by mass or more, 0.5% by mass or more, 1% by mass or more, 2% by mass or more, 5% by mass or more, 10% by mass or more, or about 15% by mass or more.
- the amount of the lipid-peptide compound as a percent of the entire composition can be, for example, 20% by mass or less, 10% by mass or less, 7% by mass or less, 5% by mass or less, 3% by mass or less, 2% by mass or less, or 1% by mass or less.
- the bacterial repelling composition may further contain a bactericidal agent.
- the bactericidal agent include cationic surfactants such as benzalkonium chloride, benzethonium chloride, and cetylpyridinium chloride; biguanide compounds such as chlorhexidine gluconate, and chlorhexidine hydrochloride; iodine-based compounds such as iodine ion, iodoform, and povidone iodine; inorganic compounds such as a silver compound that generates a silver ion; phenol-based compounds such as cresol and isopropylmethylphenol, parabens such as methylparaben, benzoic acid, and salts thereof.
- cationic surfactants such as benzalkonium chloride, benzethonium chloride, and cetylpyridinium chloride
- biguanide compounds such as chlorhexidine gluconate, and chlorhexidine hydrochloride
- the bactericidal agents can be used alone or can be used by combining two or more of them.
- the blending amount of the bactericidal agent can be, for example, totally about 0.001% by mass or more, about 0.01% by mass or more, or 0.05% by mass or more, and about 10% by mass or less, about 5% by mass or less, or about 1% by mass or less, based on the total amount of the bactericidal agent.
- the bacterial repelling composition may further contain an anti-inflammatory agent or an antiphologistic agent.
- anti-inflammatory agent or an antiphologistic agent include glycyrrhizic acid and a derivative thereof, a glycyrrhetic acid derivative, salicylic acid derivative, hinokitiol, guaiazulene, allantoin, indomethacin, ketoprofen, ibuprofen, diclofenac, loxoprofen, celecoxib, infliximab, etanercept, zinc oxide, hydrocortisone acetate, prednisone, diphedramine hydrochloride, chlorpheniramine maleate, plant extract (e.g.
- the anti inflammatory agents or the antiphologistic agents can be used alone or can be used by combining two or more of them.
- the blending amount of the anti-inflammatory agent or the antiphologistic agent can be, for example, totally about 0.001% by mass or more, about 0.01% by mass or more, or about 0.05% by mass or more, and about 10% by mass or less, about 5% by mass or less, or about 2% by mass or less, based on the total mass of the bacterial repelling composition.
- the bacterial repelling composition may further contain a calcium phosphate compound.
- the calcium phosphate compound functions as a dentin-strengthening agent that promotes remineralization when used in dental use. Calcium phosphate also functions as a polishing agent in some cases. Examples of the calcium phosphate include tricalcium a-phosphate, tricalcium b-phosphate, tetracalcium phosphate, hydroxyapatite and the like.
- the calcium phosphate compounds can be used alone or can be used by combining two or more of them.
- the blending amount of the calcium phosphate compound can be, for example, about 0.001% by mass or more, about 0.01% by mass or more, or about 0.05% by mass or more, and about 1% by mass or less, about 0.5% by mass or less, or about 0.1% by mass or less, based on the total mass of the bacterial repelling composition.
- the bacterial repelling composition may further contain long-chain
- alkylhydroxycarboxylic acid or a salt thereof When the calcium phosphate compound is further added to the composition containing the bactericidal agent and/or the anti- inflammatory agent or the antiphologistic agent at the high concentration, addition of long- chain alkylhydroxy carboxylic acid or a salt thereof promotes self-organization of the lipid- peptide compound, thereby, dispersibility of the calcium phosphate compound can be more enhanced.
- the long-chain alkylhydroxy carboxylic acid or a salt thereof include mono-, di-, tri-, or tetra-hydroxycarboxylic acid in which the number of carbon atoms of an alkyl chain is 9 to 23, and salts of an alkali metal such as sodium and potassium thereof.
- Examples of such long-chain alkylhydroxycarboxylic acid include 12- hydroxystearic acid.
- the long-chain alkylhydroxycarboxylic acids can be used alone or can be used by combining two or more of them.
- the blending amount of the long-chain alkylhydroxycarboxylic acid can be, for example, totally about 0.01% by mass or more, about 0.1% by mass or more, or about 1% by mass or more, and about 20% by mass or less, about 10% by mass or less, or about 5% by mass or less, based on the total mass of the bacterial repelling composition.
- the bacterial repelling composition may further contain a solvent.
- a solvent polar solvents such as water, ethanol and isopropanol can be used. The solvents can be used alone or can be used by combining two or more of them.
- the solvent contains water, and the bacterial repelling composition is an aqueous composition. Water may be purified water.
- the content of the solvent can be, for example, about 30% by mass or more, about 50% by mass or more, or about 70% by mass or more, and about 95% by mass or less, about 90% by mass or less, or about 80% by mass or less, based on the total mass of the bacterial repelling composition.
- the bacterial repelling composition may contain an abrasive.
- the abrasive include calcium hydrogen phosphate, aluminum hydroxide, silicic anhydride, calcium carbonate, and the like.
- the abrasives can be used alone or can be used by combining two or more of them.
- the blending amount of the abrasive can be, for example, totally about 1% by mass or more, about 10% by mass or more, or about 20% by mass or more, about 50% by mass or less, about 40% by mass or less, or about 30% by mass or less, based on the total mass of the bacterial repelling composition.
- the bacterial repelling composition may contain a binder or a thickener.
- binder or the thickener examples include, for example, water-soluble
- the binders or the thickeners can be used alone or can be used by combining two or more of them.
- the blending amount of the binder or the thickener can be, for example, totally about 0.01% by mass or more, about 0.05% by mass or more, or about 0.1% by mass or more, and about 15% by mass or less, about 10% by mass or less, or about 5% by mass or less, based on the total mass of the bacterial repelling composition.
- the bacterial repelling composition may contain a wetting agent.
- the wetting agent include, for example, polyhydric alcohols such as ethylene glycol, propylene glycol, dipropylene glycol, 1, 3-butylene glycol, 1, 4-butylene glycol, pentylene glycol, hexylene glycol, isoprene glycol, ethylhexanediol, isopentyldiol, glycerin, diglycerin, polyglycerin, sorbitol, xylitol, maltitol, mannitol, and erythritol.
- the wetting agents can be used alone or can be used by combining two or more of them.
- the blending amount of the wetting agent can be, for example, totally about 0.1% by mass or more, about 1% by mass or more, or about 5% by mass or more, and about 40% by mass or less, about 30% by mass or less, or about 20% by mass or less, based on the total mass of the bacterial repelling composition.
- the bacterial repelling composition may contain additives which are used in the known external agents, in addition to the above-mentioned ingredients.
- the additive examples include, for example, foaming agents, aerosol agents, organic acids, antioxidants, ultraviolet absorbing agents, stabilizers, antiseptics, metal ion sequestering agents, pH adjusting agents, corrigents, flavorants (flavor agents), coloring matters, whitening agents, vitamins, and the like.
- the bacterial repelling composition can be prepared, for example, by the following procedure, being not limiting.
- Purified water at 80°C is prepared. To purified water are appropriately added a wetting agent such as glycerin, a pH adjusting agent such as sodium hydroxide, a bactericidal agent such as cetylpyridinium chloride, an anti-inflammatory agent such as dicalcium glycyrrhizinate, and the like, and the materials are dissolved.
- a wetting agent such as glycerin
- a pH adjusting agent such as sodium hydroxide
- a bactericidal agent such as cetylpyridinium chloride
- an anti-inflammatory agent such as dicalcium glycyrrhizinate, and the like
- Additives such as stearic acid, sodium hydroxide, and l,3-butanediol are appropriately added to the mixture, and the materials are dissolved.
- the lipid-peptide compound can also be used by preparing it in the form of a lipid-peptide compound-containing premix (solid matter containing a lipid-peptide compound, and additives such as stearic acid, sodium hydroxide, and l,3-butanediol).
- a lipid-peptide compound-containing premix solid matter containing a lipid-peptide compound, and additives such as stearic acid, sodium hydroxide, and l,3-butanediol.
- the lipid-peptide compound-containing premix is heated to 80°C or higher and dissolved, the solution is added to purified water prepared at 1, and the resulting mixture is heated at 80°C.
- aqueous solution containing a binder or a thickener such as a carboxyvinyl polymer is appropriately added a suitable amount of water, this is added to the above-mentioned mixture in which the lipid-peptide compound has been dissolved, and the materials are further mixed while heating to 80°C or higher.
- the mixture obtained at 4 is cooled while stirring with a Homo Disper emulsifying device (400 to 600 rpm), to form a structure of a self-organized lipid-peptide compound, thereby, a bacterial repelling composition is prepared.
- a bacterial repelling coating can be formed on those surfaces.
- a method of applying the bacterial repelling composition include coating, immersion, and spraying using a finger, a roller, a brush, a sponge or the like. After application of the bacterial repelling composition, the solvent may be removed by heating.
- the bacterial repelling composition can be used in a variety of intended uses.
- the bacterial repelling composition is used in dental use in the form of dentrifice, liquid dentrifice, varnish or mouthwash.
- Dental plaque that is the community of a microorganism, for example, Streptococcus mutans, which is seen in the oral cavity, is widely known as the main cause for dental caries and other oral infection.
- the base material was placed into and taken out from the liquid until blue was not dissolved out with a decoloring liquid.
- the magnitude of the absorbance is proportional to an amount of bacteria attached to the base material surface.
- a bacterial repelling composition was prepared as follows:
- lipid-peptide compound-containing premix product name, NANOFIB ERGEL (registered trademark) TW-01W, NISSAN CHEMICAL INDUSTRIES, LTD., Chiyoda-ku, Tokyo, Japan
- the lipid- peptide compound-containing premix contains 4% of Palmitoyl Dipeptide- 18 (palmitoyl- Gly-His) which is a lipid-peptide compound, 1% of stearic acid, 0.48% of sodium hydroxide, 40% of l,3-butanediol, and 54.52% of water.
- the mixture obtained at 2 was cooled while stirring (400 to 600 rpm) with a Homo Disper (Model 2.5, PRIMIX Corporation, Awaji-shi, Hyogo-ken, Japan), to form a structure of a self-organized lipid-peptide compound, thereby, a bacterial repelling composition was obtained.
- a Homo Disper Model 2.5, PRIMIX Corporation, Awaji-shi, Hyogo-ken, Japan
- the average absorbance is expressed as a relative value, letting the absorbance of an example as a standard in the table to be 100.
- a bacterial repelling composition was prepared as follows:
- lipid-peptide compound- containing premix product name, NANOFIB ERGEL (registered trademark) TW-01W, NISSAN CHEMICAL INDUSTRIES, LTD., Chiyoda-ku, Tokyo, Japan
- a lipid-peptide compound- containing premix product name, NANOFIB ERGEL (registered trademark) TW-01W, NISSAN CHEMICAL INDUSTRIES, LTD., Chiyoda-ku, Tokyo, Japan
- a bacterial repelling composition was prepared as follows:
- Example 8 and Example 9 had the same composition, and Example 8 was applied as it was to the base material surface, and Example 9 was shaken vigorously with a hand for 5 seconds immediately before application to the base material surface.
- Example 8 aggregates existed in the resulting composition (gel) (visual observation).
- the bacterial repelling composition of Example 9 aggregates in the gel disappeared by shaking.
- the average absorbance is expressed as a relative value, letting the absorbance of an example as a standard in the table to be 100.
- a bacterial repelling composition was prepared as follows:
- bacterial repelling property assessment test was performed, and the resulting average absorbance, dispersibility and the result of observation of the state of the composition are shown in Table 4.
- the absorbance is expressed as a relative value, letting the absorbance of an example as a standard in the table to be 100. For Examples 10 to 12, since a uniform composition was not obtained, bacterial repelling property assessment was not performed.
- bacterial repelling compositions were prepared as follows:
- the lipid-peptide compound premix had been heated to 80°C or higher and dissolved, and the resulting mixture was heated at 80°C.
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JP2024042716A (ja) * | 2021-02-05 | 2024-03-29 | 日産化学株式会社 | 布類又は紙類汚染防止材料 |
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WO2001098362A2 (en) * | 2000-06-16 | 2001-12-27 | Hercules Incorporated | Chemically-modified antimicrobial peptides, compositions and methods of production and use |
JP2009523890A (ja) | 2006-01-18 | 2009-06-25 | ハイドロマー インコーポレイテッド | 微生物付着防止用の非浸出性表面活性フィルム組成物 |
JP2011153101A (ja) | 2010-01-28 | 2011-08-11 | Nof Corp | 口腔用微生物付着防止剤 |
EP2700691A1 (en) * | 2011-04-22 | 2014-02-26 | Nissan Chemical Industries, Ltd. | Hydrogel-forming material |
JP2016175956A (ja) | 2015-03-18 | 2016-10-06 | 三菱エンジニアリングプラスチックス株式会社 | 撥菌材 |
EP3210613A1 (en) * | 2014-06-30 | 2017-08-30 | Rohto Pharmaceutical Co., Ltd. | Composition for external application |
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WO2001098362A2 (en) * | 2000-06-16 | 2001-12-27 | Hercules Incorporated | Chemically-modified antimicrobial peptides, compositions and methods of production and use |
JP2009523890A (ja) | 2006-01-18 | 2009-06-25 | ハイドロマー インコーポレイテッド | 微生物付着防止用の非浸出性表面活性フィルム組成物 |
JP2011153101A (ja) | 2010-01-28 | 2011-08-11 | Nof Corp | 口腔用微生物付着防止剤 |
EP2700691A1 (en) * | 2011-04-22 | 2014-02-26 | Nissan Chemical Industries, Ltd. | Hydrogel-forming material |
EP3210613A1 (en) * | 2014-06-30 | 2017-08-30 | Rohto Pharmaceutical Co., Ltd. | Composition for external application |
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CN114846108A (zh) * | 2019-12-26 | 2022-08-02 | 日产化学株式会社 | 防污染材料 |
EP4074380A4 (en) * | 2019-12-26 | 2023-02-15 | Nissan Chemical Corporation | ANTI-POLLUTION MATERIAL |
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